1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 25235904, compound

HRID 1360744Notes

Reaction equation

HRID 1360744 reaction equation
N1(C(N2C=CN=C2)=S)C=CN=[CH:2]1.[CH:13]12[CH2:19][CH:16]([CH2:17][CH2:18]1)[CH2:15][CH:14]2[NH2:20].[Cl:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[C:23]=1[C:29]1[NH:30][C:31]2[CH:37]=[C:36]([C:38]([NH:40][NH2:41])=[O:39])[CH:35]=[CH:34][C:32]=2[N:33]=1.CCN=C=NCCCN(C)C>CN(C=O)C.O>[CH:13]12[CH2:19][CH:16]([CH2:17][CH2:18]1)[CH2:15][CH:14]2[NH:20][C:2]1[O:39][C:38]([C:36]2[CH:35]=[CH:34][C:32]3[N:33]=[C:29]([C:23]4[C:24]([Cl:28])=[CH:25][CH:26]=[CH:27][C:22]=4[Cl:21])[NH:30][C:31]=3[CH:37]=2)=[N:40][N:41]=1

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 802641,1'-ThiocarbonyldiimidazoleHCID 98480Exo-2-bornanamineHCID 577865852-(2,6-Dichloro-phenyl)-3H-benzoimidazole-5-carboxylic acid hydrazide

Product 1

HCID 25235904HCID 25235904, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
80 °C

Procedure

Add di-imidazol-1-yl-methanethione (72 mg, 0.403 mmol) to a solution of bicyclo[2.2.1]hept-2-ylamine (48 uL, 0.403 mmol) in DMF (1 mL) and stir for 3 hr. Add 2-(2,6-dichloro-phenyl)-3H-benzoimidazole-5-carboxylic acid hydrazide (100 mg, 0.310 mmol) and DMF (1 mL) to the reaction. Heat the mixture to 80° C. for 1.5 hr. Add EDCI (119 mg, 0.620 mmol) and heat for 1 hr. Allow the reaction to cool to room temp and dilute with water (15 mL). Collect the resulting precipitate by filtration. Suspend the solid in boiling ACN. Allow the suspension to cool to room temp and then 4° C. Filter to collect the white solid. Suspend the solid in 1 N NaOH (3 mL) and stir for 20 min. Filter and wash the solid with 1 N NaOH, water, and Et2O. Dry the solid in a vac oven to afford the title compound as a white solid: 1H NMR (400 MHz, MeOD) δ ppm 1.17-1.35 (m, 3H) 1.42-1.49 (m, 1H) 1.50-1.64 (m, 3H) 1.87 (ddd, J=12.98, 8.05, 2.08 Hz, 1H) 2.33 (br. s., 1H) 2.40 (d, J=4.04 Hz, 1H) 3.54 (dd, J=7.77, 2.84 Hz, 1H) 7.55-7.63 (m, 3H) 7.77 (d, J=8.34 Hz, 1H) 7.92 (dd, J=8.53, 1.20 Hz, 1H) 8.17 (s, 1H); MS (m/z) 439.9 (M+1).

Workup

  1. customthe reaction
  2. temperatureto cool to room temp
  3. customCollect the resulting precipitate
  4. filtrationby filtration
  5. temperatureto cool to room temp
  6. custom4° C
  7. filtrationFilter
  8. customto collect the white solid
  9. stirringstir for 20 min
  10. filtrationFilter
  11. washwash the solid with 1 N NaOH, water, and Et2O
  12. customDry the solid in a vac oven

Sources & evidence

ORD record
ord-5a9a0681f6084dd780ca513c4ca9fcf7
Source dataset
uspto-grants-2011_02
Patent number
US07879850B2

Reaction notes

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